Sesamol

Modify Date: 2024-01-02 20:20:33

Sesamol Structure
Sesamol structure
 Common Name Sesamol
CAS Number 533-31-3 Molecular Weight 138.121
Density 1.4±0.1 g/cm3 Boiling Point 274.0±29.0 °C at 760 mmHg
Molecular Formula C7H6O3 Melting Point 62-65 °C(lit.)
MSDS Chinese USA Flash Point 119.5±24.3 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Sesamol


Sesamol is a constituent of sesame oil. Sesamol shows a free radical scavenging activity. Sesamol shows an IC50=5.95±0.56 μg/mL in the DPPH assay. Anti-oxidant activities[1]. Anticancer activities[2].

 Names

Name 1,3-benzodioxol-5-ol
Synonym More Synonyms

 Sesamol Biological Activity

Description Sesamol is a constituent of sesame oil. Sesamol shows a free radical scavenging activity. Sesamol shows an IC50=5.95±0.56 μg/mL in the DPPH assay. Anti-oxidant activities[1]. Anticancer activities[2].
Related Catalog
In Vitro Sesamol has also been shown to be a classical inhibitor of lipid peroxidation[1]. Sesamol (0-1 mM) efficiently induces the apoptosis of human liver hepatocellular carcinoma (HepG2) cells. Sesamol suppresses cell proliferation and induces intrinsic and extrinsic apoptosis in HepG2 cells. Sesamol treatment elicites mitochondrial dysfunction by inducing a loss of mitochondrial membrane potential. Sesamol inhibits mitophagy and autophagy through impeding the PI3K Class III/Belin-1 pathway. Sesamol decreases the expression of anti-apoptotic protein Bcl-2, but shows no effect on the expression of apoptotic signal Bax. Sesamol improves the protein expression of Fas/FasL, and activates tBid and caspase-8 which are all involved in the extrinsic apoptosis pathway[2].
In Vivo Sesamol treatment for 35 days does not significantly impact body weight, although the tumor volume is dramatically inhibited (40.56% size inhibitory rate with Sesamol at 200 mg/kg compared to the control group). However, a lower dose (100 mg/kg Sesamol) only has significant anti-tumor growth effect up to 27 days after the first treatment. The Bcl-2/Bax ratio in tumor tissues is also decreased. Moreover, in the Sesamol treatment group, levels of the cell proliferation marker Ki76 are down-regulated, and levels of the cell apoptosis marker cleaved-caspase 3 are increased when compared to control. The expression of LC3 protein is remarkably decreased by Sesamol in a dose-dependent manner[2]
References

[1]. Kapadia GJ, et al. Chemopreventive effect of resveratrol, sesamol, sesame oil and sunflower oil in the Epstein-Barrvirus early antigen activation assay and the mouse skin two-stage carcinogenesis. Pharmacol Res. 2002 Jun;45(6):499-505.

[2]. Liu Z, et al. Sesamol Induces Human Hepatocellular Carcinoma Cells Apoptosis by Impairing MitochondrialFunction and Suppressing Autophagy. Sci Rep. 2017 Apr 4;7:45728.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 274.0±29.0 °C at 760 mmHg
Melting Point 62-65 °C(lit.)
Molecular Formula C7H6O3
Molecular Weight 138.121
Flash Point 119.5±24.3 °C
Exact Mass 138.031693
PSA 38.69000
LogP 1.52
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.609
Storage condition −20°C
Water Solubility slightly soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SM0890000
CHEMICAL NAME :
Phenol, 3,4-(methylenedioxy)-
CAS REGISTRY NUMBER :
533-31-3
BEILSTEIN REFERENCE NO. :
0127405
LAST UPDATED :
199709
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C7-H6-O3
MOLECULAR WEIGHT :
138.13
WISWESSER LINE NOTATION :
T56 BO DO CHJ GQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
874 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors
REFERENCE :
JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 83,1279,1992
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1092 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors
REFERENCE :
JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 83,1279,1992
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1612 gm/kg/96W-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors
REFERENCE :
JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 81,207,1990
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1092 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors
REFERENCE :
JJCREP Japanese Journal of Cancer Research. (Elsevier Science Pub. BV, POB 211, 1000 AE Amsterdam, Netherlands) V.76- 1985- Volume(issue)/page/year: 81,207,1990

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant
Risk Phrases R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS SM0890000
HS Code 2932999099

 Synthetic Route

 Customs

HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles26

More Articles
Synthesis and photopolymerization kinetics of benzophenone sesamol one-component photoinitiator.

Photochem. Photobiol. Sci. 12(2) , 323-9, (2013)

A benzodioxole derivative, 4-(2-(benzodioxol-5-yloxy)ethoxy)benzophenone (BPC2BDO), based on 4-hydroxybenzophenone and sesamol was synthesized, and used as a one-component Type II photoinitiator. The ...
Comparison of the simple cyclic voltammetry (CV) and DPPH assays for the determination of antioxidant capacity of active principles.

Molecules 17(5) , 5126-38, (2012)

Antioxidant activity of a number of small (low molecular weight) natural compounds found in spices, condiments or drugs (gallic acid, sesamol, eugenol, thymol, carvacrol, vanillin, salicylaldehyde, li...
The interaction of sesamol with DNA and cytotoxicity, apoptosis, and localization in HepG2 cells.

Food Chem. 141(1) , 289-96, (2013)

Sesamol, a nutritional antioxidant phenolic compound present in sesame seed, has a potential therapeutic molecule effect against cancers. In this study, the interaction between sesamol and DNA was inv...

 Synonyms

5-Benzodioxolol
MFCD00005827
5-Hydroxy-1,3-benzodioxole
EINECS 208-561-5
Phenol, 3,4- (methylenedioxy)-
Sesamol
4,5-methylenedioxyphenol
3,4-Methylenedioxyphenol
1-hydroxy-3,4-methylenedioxybenzene
4-hydroxy-1,2-methylenedioxy-benzene
5-hydroxy-1,3-benzodioxolane
3,4-(Methylenedioxy)phenol
Methylene ether of oxyhydroquinone
1,3-benzodioxol-5-ol
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Sesamol
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111726-43-3
5-Brom-sesamol
66799-94-8
methyl sesamol
7228-35-5
sesamol radical
62266-17-5
sesamol acetate
165459-70-1
sesamol acetate
326-58-9
O-Geranyl-sesamol
27927-80-6
Chemsrc provides Sesamol(CAS#:533-31-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Sesamol are included as well.>> amp version: Sesamol

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